I Choose You!
by ShockHorrorRainbowLove
Summary: Dean starts his journey as a Pokémon trainer! NC-17 Wincest/Destiel/Sabriel
1. Chapter 1

**Ok, so, here's a collab between me and my gorgeous friend Maddy (castielstrenchcoat on tumblr). We hope you enjoy!**

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><p><span>Chapter 1<span>

Pallet Town. 1999. Dean Winchester has finally decided to venture out into the wide world of Pokémon, with the help of Professor Gabriel Oak's apprentice, Sam Winchester, his nerdy younger brother.

It's the night before he has to leave, and he and Sam are in their respective beds, facing each other in the darkness.

"I'm gonna miss you, Sammy," Dean whispered across the room, breaking the silence.

Sam sniffs. "I'll miss you too, Dean," he says, letting a single tear dribble down his face and onto the pillow below.

"I'll come back to visit you all the time!" Dean reassures, slipping out of bed to tip-toe to his brothers side. "You can always count on me, Sammy." Dean knelt down in front of Sam's bed, slowly leaning forward to press a soft, lingering kiss to his lips. As Dean moved back, Sam leaned forward, not willing to break the spell surrounding them, causing Dean to chuckle under his breath. He silently pushed Sam backwards, so he was lying on his back on the centre of the bed, and crawled on top of him, straddling his hips, kissing him all the while.

After a lot of lazy kisses were shared, Dean started flowing his passion for Sam into the kiss, feeling his brothers dick harden through his thin pyjama pants.

Dean let out a bark of harsh laughter. "Metapod used Harden, eh Sammy?" Sam cocked an eyebrow.

"Shut up, Jerk," he said, craning his neck up to resume the kiss.

"Now," Dean spoke against Sam's lips, "how about I give you something to remember me by?"

Sam groaned. "Oh, God yes." Dean grinned, gently thrusting his hips down, making Sam let out a soft whine. "Please, Dean, no teasing." Dean groaned at the weak, submissive tone, finally pushing down hard, causing unbelievable friction. They both let out loud moans, reveling in the pleasure rushing through their veins. Dean quickly pulled down Sam's pants, letting Sam pull off his own.

Frantically, they rubbed against each other, the slide of their cocks making them cry out, using the pre-come from the weeping heads of their dicks as lube. Dean brought three fingers up too Sam's mouth.

"Suck," he said in a hoarse voice. Sam immediately obeyed, bringing the fingers into his mouth, and swirling his tongue around them, moaning like a back-alley whore. Once Dean considered his fingers wet enough, he removed them from Sam's mouth, bringing them down between his legs. He rubbed his pointer finger at Sam's entrance insistently. Sam whined and jerked, the pressure constantly building as he thrust his hips down, desperate for penetration. Dean smirked, finally obliging.

He quickly shoved his finger in to the knuckle, forcing his lips onto Sam's to muffle his cry. After a couple of seconds of stillness to let Sam adjust, Dean slowly began to move his finger. Thrusting in and out, barely grazing Sam's prostate, making him whimper and slowly melt under Dean's ministrations. Dean gently inserted finger after finger, scissoring and stretching, until Sam was ready for the girth of his dick. He pulled his fingers out, spitting on his hand and smearing the saliva on his dick.

Dean leant down and guided his penis with his hand, gently rubbing as Sam's entrance. With one smooth thrust, Dean was in Sam to the hilt, covering Sam's mouth with his own to muffle their groans of pleasure.

"Fuck, Sammy, how are you still this tight?" Dean whispered against Sam's plump, kiss-swollen lips. Sam whined, a pitiful sound in the back of his throat, and bucked his hips, needing Dean to move. Dean slowly pulled out, until he was only half way in, before thrusting back in full force. Sam moaned, and wrapped his legs around Dean's waist for a better angle.

Dean swore, moving his hips faster and enclosing Sam's cock in his fist, stroking in time to his thrusts. They continued like this, Dean slamming against Sam's prostate, until the pressure grew too much to bear. Dean leaned down to Sam's ear.

"C'mon, Sammy. Just let go," he whispered. Sam let out an extremely high pitched note, his back arching grandly as he came across both their chests. The constricting muscles around Dean's cock were too much to bear, and he followed shortly after.

"Ca-Sam," he groaned, barely catching himself from the slip up as he came deep inside of Sam. Thankfully, Sam was still caught up in the aftershocks of the intense orgasm to notice.

They caught their breath, Dean pulling out and laying beside Sam as they curled around each other.

"I'll miss you, Sammy." Dean said. He looked down at his brother, already peacefully asleep, and let a single tear fall into Sam's hair, letting sleep claim him quickly.

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><p>Dean woke up hazily, barely registering the curled up form of his little brother against his side. He rubbed his eyes and looked at the clock on the table, which was shaped like his favourite Pokémon, a Blastoise. "Son of a bitch" he growled as he hopped out of bed, hurriedly grabbing clothes out of his drawer and pulling them on. He heard stirring behind him.<p>

"Dean?" Sam yawned, his hair tousled and his eyes bleary.

"Sammy, we're late to meet Professor Gabriel!"

Quick as a flash, Sam hopped out of his bed and pulled on the nearest pair of jeans he could find. Barely glancing in the mirror before pulling a comb through his hair and opening the door. "There won't be any starter Pokémon left for you, we have to go now!"

Dean picked up his backpack and ran out of the door, stopping only to grab a cookie from beside the fridge, freshly made by his mother, Ellen. He skids to a halt in front of the Pokémon Lab, Sam just behind him.

"Good luck" Sam says bracingly, pushing Dean forward and through the door. Dean slowly walks through the auditorium, the place silent apart from his footsteps. It seems like hours before he reaches Prof. Gabriel's door. He takes a deep breath and knocks on it. The door opened almost immediately and Dean was stood, almost nose to nose, with Castiel Novak, Gabriel's nephew. He held his breath. He had always had some sort of fixation with the boy, no matter how cold and distant he was. Looking into Castiel's deep, sea blue eyes he cleared his throat.

"Oh uh, hey Castiel. Is your uncle Gabe in?"

"You're late." Castiel said simply, turning around and walking over to a table in the corner of the room, perching himself on it. Dean walked in, an awkward silence hung in the air. He must admit though, Castiel's ass looked fantastic in those jeans. As Castiel opened his mouth to say something, Professor Gabriel walked in to the room, with a lollipop in one hand and a Pokéball in the other.

"Oh, Dean, you've finally decided to join us," he said sarcastically.

"Sorry Gabriel, I woke up late, my mom didn't bother to wake me up this morning."

"No harm done, however, most of the Pokémon we had up for grabs today have already been taken. Luckily, we do have one more." Gabriel held up the Pokéball in his hand, surveying it for a moment before throwing it to Dean, which he caught with one hand.

"Woah, thanks Gabriel, really!" Dean smiled and looked at the Pokéball. His own Pokémon! He could hardly believe it!

Just then, there was a knock at the door. Gabriel walked over to answer it.

"Why hello there, young Samuel. How the devil are you?" he said teasingly, a smile playing at the edge of his lips.

"Oh! H-hey Gabe," Sam stuttered, turning a light shade of red. "Is my brother here?"

Gabriel moved out of the way of the door and Sam walked in.

Dean smiled in greeting to Sam, stood up and took a deep breath. "Come on out, little buddy" he said, throwing the Pokéball to the floor. The Pokéball opened and in a flash of brilliant light, out came a Squirtle! Sam sighed, it was the cutest Pokémon of the bunch in his opinion. Gabriel glanced at Sam out of the corner of his eye, a smirk forming on his face. Dean huffed, the Pokémon just looked girly in his opinion. The smirk on Gabriel's face grew.

"Don't you worry, Dean," he said. "It'll evolve into something more manly for your liking soon enough." He winked, leaving Dean looking disgusted at the Pokémon he had just received. Castiel stood up and yawned, a glint in his eye. "Hey Dean, how about a battle? I'll show you how much of a pipsqueak your little Pokémon is.

"Yes, Dean, let Cassy here show you his skills." Gabriel said, a wide smile evident on his face.

Castiel rolled his eyes. "Shut up Gabe, no ones called me Cassy since I was about five years old."

"Well obviously, they still do, _Cassy._" Gabriel replied, putting emphasis on the last word.

Dean looked over at Castiel.

"Challenge accepted."

Castiel pulled a Pokéball from his belt and threw it to the ground dramatically.

"Charmander, go!"

Another dazzling flash of light and a Charmander appeared, the flame on its tail dancing in the dim light of the room. It's loud chirrup echoed through the room, sending a shiver of thrill down Dean's spine as he watched Castiel. Great. He had to get turned on _now._ By Castiel Novak, too.

Dean looked towards his new Squirtle.

"We have to work together now buddy... so uh... attack!" Squirtle waddled forward, towards Charmander.

"Charmander, use scratch!" Castiel commanded.

"Squirtle, dodge it!" Dean shouted in return.

Charmander missed Squirtle by an inch as he moved towards him, his sharp claws outstretched.

"Squirtle! You know bubble beam, right? Use it now!" Dean said imploringly, looking between Castiel and his Pokémon.

Squirtle stopped for a split second before releasing a large amount of bubbles from it's mouth, speedily sending them Charmander's way. Charmander stumbled for a second.

"Charmander! Try to get out of the stream!" Castiel bellowed. But it was too late. Charmander was down.

"What? I won?" Dean said, disbelievingly. "AWESOME! High-five, Squirtle!" Dean ran over to the half turtle, half squirrel creature and put a hand up, waiting for the Pokémon to raise its little hand up too. Squirtle seemed to consider Dean for a second before putting his tiny hand to Dean's, its lips curling up at the sides.

"You know what, little buddy? I'm sorry I doubted you. You full on swayzee'd that mother!" Dean stood up now, walking over to Castiel where he was sat with his Charmander. "Hey man, is Charmander alright?"

Castiel looked up, resentment and an emotion Dean couldn't quite register in his eyes. "Charmander'll be fine. Good work, I guess. But we're gonna train up and next time we battle each other, I'm going to win!"

Dean smiled before putting out his hand. "Deal."

Castiel took it and gave it a brief shake before turning his attention back to Charmander.

Dean walked over to his new Pokémon, bending down and picking up the Pokéball. "Come on, little guy, back in here for now!" Squirtle looked up at him.

"Squirtle!" he said cheerfully. Dean hoped this meant he wanted to go back into the ball. Dean pressed the button in the middle. "Squirtle, return!" A flash of red light and Squirtle was gone.

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><p>"Sammy? Where are you?" Dean looked around the laboratory, checking everywhere it seemed before giving up. Sam's probably just gone home, he thought to himself. As he was leaving out of the door, he heard a crash coming from Gabriel's office. Dean doubled back and walked over to the door, opening it tentatively. "Gabriel? Are you okay?" Dean entered Gabriel's office and saw that the computer that had been on the desk had crashed to the floor. Sam then appeared from the corner of the room, his hair ruffled and his lips looked red and swollen. "Sammy? What're you doing in here? I thought you'd left?"<p>

"Oh um, I was just... I-" Sam was cut off by Gabriel coming out of the store cupboard.

"Sammy here was just helping me fish out this for you, Dean." Gabriel took something square and red out of his pocket before opening it up and handing it to Dean.

"Dean, this is a Pokédex. It should help you on your journey to being a Pokémon league Champion. It has all you need to know on it. If you ever need to find out what a Pokémon is, what special attacks it has, what different evolution states it has or what level it is, refer to this."

Gabriel handed it to Dean and he turned it around in his hands gingerly. He opened it up and a robotic voice came from within. "Hi! I am Ash, your Pokédex. I will be your personal aid through your long journey. If you need anything, don't hesitate to ask." Dean looked up.

"Woah! Thanks Gabriel, this will be a great help!" he put the Pokédex in his back pocket and put his arm around his younger brother.

"We'll see you later, okay?" Dean called as he got to the door. He saw Sam and Gabriel share a fleeting glance and he swore he saw Gabriel wink at Sam a split second before the door closed.

Dean decided to shower and change his clothes before starting his journey. He got home and proudly displayed his new Pokémon to his mom, before putting it back in it's Pokéball and taking a quick shower. He stepped into the shower and let the hot water go over his body. He thought about earlier, his first ever Pokémon battle. His battle with _Castiel. _The mere thought of the man caused ripples of arousal to zing down his spine. He glanced down at his already half-hard cock, and reached down to take a firm hold of it. Images of Castiel flowed through his mind, providing plenty of inspiration. Castiel's ass in those jeans. Castiel in the midst of battle. Castiel comforting his fallen Pokémon. Just about anything he did was making Dean horny, but he still came up with his own scenes: Castiel on his knees. Castiel naked and writhing beneath him. Castiel, Castiel, Castiel.

Dean groaned, speeding up the movements of his hand to keep up with the images flashing behind his eyelids as he sped toward climax. In the brief moments before his orgasm, he pictured what Castiel's face would look like in his position. Screwed up, unable to take the pleasure.

Dean climaxed violently, his knees shaking as he came over the shower stall wall. He fell to his knees, the trembling too great to hold himself up. He sighed happily and rested his head against the glass.

Much better.

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><p><strong>TBC~<strong>


	2. Chapter 2

**Welcome, amigos, to chapter two! For those who don't know or have forgotten, this is a Supernatural/Pokémon collab between Maddy () and I () We sincerely hope you enjoy! Also, sorry for the wait. Blame me, not Maddy, for that ;D**

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><p>Dean was ready. Ready to venture into the world of Pokémon. Equipped with his newest companion, Squirtle, six Pokéballs, food, water and clean clothes, he stepped outside to begin his new life. After a tearful goodbye with his mother and a brief hug from his brother with a sworn promise to call when he got to the next city, Dean was gone. First stop; Viridian City. On the way there, Dean was very lucky in the aspect that his Squirtle was more powerful than average at the level it was at. By the time he'd gotten through the troublesome grasses of Route 1 - he seemed to attract wild Pokémon with each step - he'd already acquired himself a Pidgey and a Rattata.<p>

After stopping at the Pokémon Centre to heal his tired Pokémon, he headed onwards in his journey. He had to make the long walk through Viridian Forest. He was hoping he could catch a Weedle, as they're badass little Pokémon, in his opinion. As he made his way through the forest, his Squirtle out of its Pokéball and walking beside him, he saw something move out of the corner of his eye. A Caterpie! Dean sighed as he took out a Pokéball.

"Pidgey, come out!" he threw the Pokéball to the ground and in a flash of light, Pidgey was hovering a few inches above the floor. "Pidgey, sand-attack, we have to weaken the Caterpie!" Dean commanded, pointing towards the quivering bug Pokémon. Pidgey dive bombed the small Caterpie and used its long wings to blow sand in the Pokémon's face, half blinding it. "Okay, now, Pokéball, go!" Dean threw a Pokéball with all of his might towards the Caterpie.

With another flash of red light, the Pokémon had gotten inside and the ball started rocking from side to side. Dean held his breath. Normally, if a Pokémon isn't weak enough, it jumps back out, he thought. The Pokéball stopped wiggling and was still, it's seal in place.

"Alright! Well done Pidgey!" Dean stroked the bird Pokémon before bringing back out it's Pokéball. "Pidgey, return"

The rest of their journey to Pewter City went without incident, if you don't count the fact that Dean had to run away from a swarm of Beedrill. When he threw a rock at a Weedle in attempting to capture it; a swarm of Beedrill seemed to appear from thin air and chased Dean and Squirtle to the sign which showed their destination. 'Pewter City, THIS WAY' The sign showed and Dean took the rest of the way at a run, for one thing, he wanted to make sure the Beedrill were way off of his tail and for another, he wanted his first Pokémon badge.

Dean decided to stock up on some Potions and other things that would help him with his battle at the Pokémart. He asked the cashier about the gym leader.

"Bobby Singer his name is. Specialises in Rock Pokémon. It takes a lot of skill and training to beat him. He's been at it for years."

Dean sighed. Just his luck that the first Pokémon trainer was tough as a Sandshrews shell. The young cashier showed him to the Gym and patted him on the back.

"Good luck" he smiled as he walked away.

Dean took a deep breath. This was it, his first gym leader. He opened the door and was approached by a man in glasses and a black suit.

"Hello, Champ in the making! You're up against Bobby Singer now, the fearless leader of this gym. Have you got what it takes to defeat him and get the Boulder Badge? We'll see! Bobby has rock type Pokémon, which are weak against Water and Grass type Pokémon. Good luck!"

Dean sighed in relief. He had a Squirtle, a water type Pokémon! _This should be a piece of cake!_ he thought to himself, grinning. He walked through the entrance and came to a door. "Bobby Singer" was written on it in bold letters. Taking a deep breath he knocked and opened the door. A man in his late 50's with a red flannel top on, ratty jeans and a baseball cap on looked up from where he was sat. Dean blinked.

"Hello. Are you Bobby Singer, the Gym Leader here?"

"Can you not read the door you idjit?" said the man, getting to his feet and stretching.

"Yeah, I'm sorry. I'm looking for my first badge. Any chance we could battle?"

Bobby considered Dean for a moment, looking into his deep, green eyes.

"You seem like a well adjusted kid. Just don't cry too much when I beat ya." he said, getting a Pokéball off of his belt.

Dean took the bag off of his back and pulled a Pokéball from the side pocket.

"Come on out, Geodude!" Bobby said, throwing the ball and with a flourish, Geodude was ready and raring to go. Dean got out his Pokédex.

"Geodude. The rock Pokémon. It has a hard head and a sturdy body. Throwing rocks is a common type of offense by Geodude. As Geodude is also a Ground-type, it can use moves like Earthquake. Geodude also possesses the ability to explode. The blast causing severe distress." Dean sighed and put his Pokédex away. Just his luck, this Pokémon has the exploding capabilities of a nuclear bomb. Dean threw his Pokéball. "Squirtle, I choose you!"

The match had begun.

Dean gaped at Bobby's Geodude. Never had he seen such a mean looking Pokémon.

"Geodude, use Tackle!" Bobby commanded. Geodude sped towards Squirtle.

"Squirtle, counter it and use water gun!" Dean shouted. He had to admit, Squirtle was very fast on its feet even though it didn't look it. Squirtle dodged the attack and whirled around, a vast spray of water gushing from it's mouth, hitting Geodude square in the face.

"Geodude, hold on!" Bobby shouted, clenching his fists and grinding his teeth. Geodude wavered for a moment before pressing against the blast of water, forcing itself forward.

"Squirtle, Tackle him, now!"

Squirtle seemed to glow for a second before launching himself onto Geodude, forcing him to the ground with a crash.

"Geodude? Are you okay?" Bobby questioned, running over to his Pokémon. Geodude was laying there, the force of the impact making a dent in the hard ground. It had been knocked out.

"Damnit. Geodude, return!" Bobby sighed, pressing the middle of the Pokéball.

"My next Pokémon! Onix, come on out!" Bobby threw the ball to the floor and with a flash of light, out gleamed an Onix, 8 metres high, leering down on the small Squirtle.

"You gonna keep that Pokémon, idjit?" Bobby smirked, clearly pleased with his choice in Pokémon. Dean grimaced. Bobby was right. Squirtle didn't look like he stood a chance against Onix, being only half a metre tall.

Just then, Squirtle began to glow again. At first it was only faintly, then it got brighter and brighter until the whole room was engulfed in the bright light. Then, as quickly as it had started, the light dimmed and stood in Squirtle's place was a Wartortle. Considerably more manly, Dean thought to himself as he looked at the creature. He pulled out his Pokédex to see what was up.

"Wartortle, the water Pokémon. Wartortle is the evolved form of Squirtle. Wartortle are loyal to their trainers. They are also more aggressive than Squirtle. They tend to hide in water when hunting and emerge to surprise their prey. They are known to be very tough Pokémon that often have scratches on their shell which serve as reminders of past battles."

Wartortle waddled over to him and put a small hand up. Dean smiled as it reminded him of the first time he'd met his Squirtle, now Wartortle. Dean put his hand against Wartortle's and grinned. "You okay, buddy?"

Wartortle smiled appreciatively and turned around, his stance low, ready for battle.

"What a touching moment. Now time to watch my Onix crush your Pokémon." Bobby called over.

"You can try!" Dean called back, winking. "Okay, Wartortle, think strategy." Dean whispered, crouching down towards the Pokémon. "We gotta try to get Onix down to your height." Wartortle nodded, showing he understood. Dean straightened up.

"Onix, use Bind!" Bobby cried. Onix moved towards Wartortle slowly, threateningly. Just as it was about to curl Wartortle in a crushing embrace, Wartortle jumped out of the way, running up the Onix's back and settling itself on its head.

"Good one Wartortle, now, use Water Gun!" Dean screeched, in a manly fashion. Wartortle hesitated a second, and it was a second too late as Onix thrust his head backwards, sending Wartortle flying. He hit the wall with a dull thud.

"Wartortle!Are you okay?" Dean shouted, running over to his injured Pokémon. It's eyes were closed but it was still breathing. "Dude are you gonna be ok? We're gonna take you to the Pokémon centre and fix you up real good, you hear me?" Dean picked up his fallen Pokémon and got its Pokéball. "Return and have a good rest before we can get you checked out." he said. He turned towards Bobby who was stood there waiting.

"Pidgey, I choose you!" Dean threw the Pokéball to the floor and in a burst of light, Pidgey was flying around the room.

"Pidgey, use sand attack!" Dean commanded, his voice tight. Pidgey obliged and sent a burst of sand into Onix's eyes. It thrashed about uselessly, hardly able to see.

"Pidgey, use gust!"

Pidgey flapped his wings fast, making a hard, strong wind appear. However, it wasn't that effective against the Onix, and it only did a minimal amount of damage.

"Onix, bind the bird!" Bobby shouted, and Onix obeyed. Getting Pidgey in a crushing embrace, Onix began to squeeze. Dean tried to command Pidgey out of the bind, but it was no use, he was well and truly trapped. Eventually though, Onix released Pidgey, but not before he had lost a substantial amount of health. Dean dug through his backpack, looking for something that could be of use to the weak Pokémon. In it, he found a Super Potion! He now had a debate. Re-release Wartortle and use it on him, or use it on the already weak Pidgey, who was weak against Rock type Pokémon? He picked up the Pokéball in which Wartortle resided.

"Pidgey, return!" in a flash of light, Pidgey was gone.

"The rule was two Pokémon each, you idjit. You admit defeat?" Bobby leered, stroking his beard.

"Of course I don't." Dean said through gritted teeth. He needed the Boulder Badge. He imagined how proud his little brother would be of him when he told him. He wanted to prove he was a decent trainer, to his brother, Castiel and to himself. He looked down at the Pokéball in his hand. "Wartortle, go!" Wartortle came back out, stumbled a few short steps and fell down again. Dean rushed over to him and sprayed his injuries with the Super Potion, not stopping until each one was covered. They seemed to heal before his eyes and before he knew it, Wartortle was back on his feet. "Come on buddio, we have to win this!"

Wartortle looked up, his eyes filled with determination.

"Onix, bind the little twerp again" Bobby shouted, almost lazily as he compared the heights of the two Pokémon, sure he would win. Onix's tail caught Wartortle in a crushing bind before he could move. Wartortle struggled against the bind before sagging. Onix brought its broad head to Wartortle's, leering down at it. Wartortle looked up into the eyes of the huge Pokémon, silently pleading it to stop.

"Wartortle! Water Gun now! As hard as you can!" Dean exclaimed. Wartortle took aim and let rip, the water hitting Onix full force in the face, downing it before it could do anything to dodge the attack. "It's down, now tackle it!" Wartortle ran full force into the head of the downed Pokémon, tackling it down even more. Wartortle jumped back up, recovering quickly.

"Onix, are you okay?" Bobby shouted. Onix didn't answer. It had been knocked out with the force of the water, weakening it and then being crushed to the floor. Dean had won.

"Balls! Onix, return!" Bobby said, resentment in his voice. "Well played, Dean. You've won the Boulder Badge. This means Pokémon will be more loyal! You earned it, well done, Dean."

Dean was ecstatic, he'd got his first badge! He thanked Bobby and walked out of the Gym, the badge pinned to the inside of his jacket. He was well on his way to becoming a great Pokémon trainer.

Dean sauntered into the Pokémon Centre, feeling ecstatic about his recent win against Bobby. He planned on healing his Pokémon and grabbing a cheeseburger, hopefully taking it back to his rented room in the centre - if a pretty girl didn't catch his eye, that is. However, before he could grab his food, something much better than any girl caught his eye, currently healing his Pokémon. One Castiel Novak, in black, horrendously tight jeans, was leaning over the counter, casually chatting to the nurse. Dean stood, entranced by the sigh before him. The perfect globes of his ass slightly wiggling towards him, taunting him.

Yet, before Dean had the opportunity to reach out and touch, Castiel stood, effectively snapping Dean out of the haze of lust that had overtaken him. Dean cautiously approached the desk, leaning against it and facing Castiel.

"Well, well, well, what do we have here, then?" he said, smirking broadly. Castiel shifted uncomfortably under the scrutiny of Dean's gaze.

"Dean," he acknowledged, nodding slightly. Dean rubbed his hand on the slight 5 o' clock shadow growing on his chin.

"Where're you staying?" he asked confidently, even though his heart was beating a mile a minute at the proximity of their chests, Castiel's clad in a tight dark shirt, his own in a thin, slightly grubby t-shirt.

Dean licked his lips, watching as Castiel's eyes darted down to watch the slow, deliberate movement. Castiel's eyes fluttered and Dean leaned forward slightly, teasing the other man.

Abruptly, Dean pulled away, making Castiel whine and jerk his body forwards.

"Catch you later, Cas," Dean whispered in a flirty tone, then turned on his heel and left, heading towards his rented room, leaving Castiel flushed and aroused. Dean's Pokémon could wait till tomorrow after something like that.

Dean hurried down to his room, not even bothering to hide the slightly noticeable bulge in the front of his worn jeans. He smirked to himself. His impromptu plan had gone perfectly. Except now he had an erection. _Occupational hazard, I guess, _he thought to himself, laughing slightly.

He opened the door to his room, quickly locking the door behind him, and flopped down on the single bed. Dean rolled onto his back, reaching down and palming himself through his jeans, relieving some of the pressure in his dick. He groaned, images of Castiel all hot and bothered racing through his mind. With his free hand, he swiftly unbuttoned his jeans and pulled the zipper down. Wasting no time, he shoved his hand into his boxer briefs, taking a firm hold of himself, and stroking the shaft quickly.

"Cas..." he whispered, speeding up his hand to a blur in the confines of his underwear. He grunted, raising his hips and shuffling, wiggling out of both pants and boxers. Keeping his hand on his dick, he settled into a more comfortable position, stroking slowly and smoothly, moaning loudly, letting himself go completely.

Cas walked down to his rented room, still flushed and slightly hard from his encounter with Dean. He hurriedly let himself into the single and locked himself in, heading towards the ensuite bathroom for a _very _cold shower. However, when he was about halfway across the room, he heard a loud, unmistakable moan vibrate through the walls. His eyes widened comically as he turned to face the source of the noise, the room next to his. Another moan echoed through the wall, leaving a lasting impression in his brain when he realised, with a groan, that the voice belonged to Dean.

Instantly, his cock was rock hard, aching to be touched. With a low grunt, he reached down to tentatively touch himself through his skintight jeans, still tuned in to the loud noises of obvious pleasure coming from Dean's room. He lowered himself onto his own bed, coincidentally placed against the wall that hid Dean.

Cautiously, he peeled off his trousers, briefs and socks all in one go, unceremoniously flinging them across the room. Cas wrapped his fingers around himself, creating a tight fist around his cock. The slight pain from the noose-like grip only giving him more arousal. He began to moan, flicking his wrist on every upstroke, imagining Dean, head thrown back in pleasure, mirroring his current movements.

His moans grew louder, and he knew that Dean could hear him as well. The thought make him grunt, stuttering in his movements.

Dean listened carefully as he heard moans begin to accompany his.

"Ah, Dean!" the voice yelled out, and Dean's eyes boggled. That voice was unmistakeably Castiel's, and now he knew that they were both on the same wavelength. He almost sobbed, his arousal coursing through him with an almost painful speed. Dean sped up the moves of his hand, his face contorting as he felt himself near breaking point. The familiar coil in his gut signalling how close he was. His back arched and keened, coming smoothly across his chest and stomach.

Cas heard the high pitched noise, and imagined Dean above him, arching up and coming deep inside him. The thought alone of this sent him over the edge, and he whimpered as he came, the force of the orgasm shocking him and tiring himself. He barely has enough energy to grab his t-shirt and clean himself up, and fell quickly to sleep.

Dean smirked to himself. If he'd known that Cas could be this vocal, he would've stuck around earlier. He wiped himself off with some conveniently placed tissues nearby and quickly drifted off to sleep.

Dean awoke bright and early from a dreamless sleep and walked out of his room. He'd wanted to heal his Pokémon up and call his brother to tell him how he was getting on the night before, but circumstances made that impossible. Dean walked down to the Pokémon centre and let out his Wartortle, Pidgey and Caterpie so that Nurse Mary could look at them and assess any damage they may have had inflicted by his previous match against Bobby Singer. As his Pokémon were being treated, he decided to get a spot of breakfast before calling his brother. Walking over to the café across the street, Dean ordered a large cheeseburger with fries and an apple pie. Dean loved pie. After he'd eaten, Dean made the short walk back to the Pokémon Centre, took his now healed Pokémon and went back to his room. He plopped down on his bed and pulled his phone out of his pocket, searched for Sam's name and put the phone to his ear. No answer. Dean frowned, normally Sam always had his phone on him. He called again and on the last ring, Sam picked up, sounding breathless.

"Hey Dean," Sam gasped

"Sammy! Hey! How have you been?" Dean replied, hearing his brothers familiar deep voice and smiling in spite of himself.

"I've been fine thanks, how are you getting on?"

"Dude, you won't believe it! I've got my first badge already!" Dean said excitedly.

"Oh wow! I knew you had it in you, Dean, well done!" Sam said, his voice heavy with pride. Dean heard a cough on the other end of the phone.

"Hey Dean? Listen, I have to go. I'm in the middle of something, I'll talk to you later, bye." The phone went dead. Dean looked down at his phone curiously, before shrugging and continuing on with his day.

Gabriel sighed, snaking his arms round Sam's waist, settling his hands on Sam's toned stomach.

"Saaaam, I've got a new product for us to try out," he said, with an obvious smirk in his voice.

"Let me guess, it's home-made?" Sam replied, rolling his eyes.

Gabriel kissed Sam's neck. "Isn't everything I get us to try out?"

Sam laughed, turning in Gabriel's arms and looping his arms around his neck. Gabriel leaned up onto his tip-toes and kissed Sam, snaking his tongue quickly into Sam's mouth. Sam slowly pulled away.

"C'mon then, tell me what it is," he said against Gabriel's lips.

Gabriel pulled away completely, holding up a small glass bottle. "Chocolate flavoured lube!" he shouted excitedly, making Sam's eyes boggle in his head.

"Seriously?" he asked, unsure whether Gabriel was joking or not. Gabriel nodded, grinning ear to ear. "Let's do this, then," Sam said, taking off his t-shirt, revealing his muscular chest. Gabriel looked dumbstruck, he never thought that Sam would give in so easily.

"Awesome!" he cried, stripping off his own t-shirt. Sam laughed at his enthusiasm, grabbing his hand and leading him towards the bedroom that was adjacent to Gabriel's office. Gabe sealed their lips together, forcing Sam backwards until the back of his knees hit the edge of the bed.

Sam sat down heavily, Gabriel immediately straddling his thighs, pushing his hips forward into Sam's. Sam whined, the pressure barely enough to relieve the growing tension in his groin. Gabriel smirked, pressing down harder, insistently thrusting against Sam.

"You are wearing too many clothes."

"They're just pants, Sammy." Gabe smirked.

"Yeah, well, they need to go. Now." he replied, impatience heavy in his voice. Gabriel stood, teasingly inching his dress pants down, inch by inch revealing his smooth skin. Sam huffed, and yanked down his own jeans, quickly pulling Gabriel back onto his lap. They gasped as their cocks rubbed against each others, bucking forward to get more of the delicious friction.

Gabriel groaned, shoving the bottle into Sam's hand. "Prep me, Sammy," he whispered huskily. Sam growled, popping the cap and squeezing the clear liquid onto his fingers, quickly bringing a finger up to his mouth to taste it.

"Well, you certainly for the taste," he chuckled, low in his throat so it was almost a growl. Gabriel whined and bucked forward, desperate for Sam. Sam smirked again, reaching his hand behind Gabe and circling his entrance with his pointer finger. Gabriel gasped, screwing his eyes shut and pushing back against the finger. Sam's finger gently slid passed the tight muscle and pushed inside, quickly searching for Gabriel's prostate. Gabriel jerked his body as Sam brushed against the gland, shuddering as he roughly probed it, slipping in his fingers while Gabe was distracted. By the time Sam had three fingers buried in Gabriel's ass, he was riding them, fucking himself on them relentlessly. Sam growled, Gabe looked too hot for his own good. He removed his fingers, earning a whine from Gabriel.

"Fuck me, Sam, do it now," he keened, desperate for Sam's dick. Sam groaned, quickly squeezing more lube onto his hand, rubbing it over his dick and guiding Gabriel down onto it.

As Gabriel impaled himself on Sam's cock, they both moaned loudly, the pleasure almost too much to bear.

"Gabe," Sam grunted, thrusting his hips into Gabriel.

"Sam, c'mon, fuck me, please," Gabriel cried, lifting himself up and dropping back onto Sam's lap with a shudder. Sam gripped his hips tightly, so tight he would leave bruises, and lifted him back up. He let him drop back down, but bringing his hips up halfway to slam into Gabriel's, making them groan and shudder. They continued like this, setting up a swift rhythm. Their mixed grunts and groans of pleasure echoed through the room, the only other noise was the harsh slap of skin on skin. Sweat poured off their bodies as they neared their climax. Gabriel whined and keened as Sam pummeled his prostate, grunting and groaning, low in the back of his throat.

Sam felt the familiar coil in his belly and wrapped a strong hand around Gabriel's dick, stroking him to the edge of his orgasm.

"Gabe," Sam ordered in a husky voice, demanding Gabriel look at him. "Come for me, Gabe."

That was all the encouragement he needed. His back curved graciously as his muscles tightened, and he came all over both their chests. His ass tightened around Sam's dick, the pressure just enough to send him over the brink, coming deep inside Gabriel's ass. They shuddered and clung to each other, feeling as though they would break or loose each other if they dared to let go. After they'd come down from their highs, Gabriel smirked at Sam.

"Time for a taste test, me thinks, Sammykins," he said with a wink. He dismounted off of Sam's lap, and leant down to neatly lick at Sam's dick, wiping off any left over come or lube. Once Sam's cock was clean, he sat back up, licking his lips and smiling. "Oh, I definitely got the taste, Sammy."

Sam threw his head back and laughed. They would definitely be doing that again.

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><p><strong>TBC~<strong>

**P.S. please review, so we know if we sucked or not. muchos love**


	3. Chapter 3

**Another day, another chapter! Maddy (castielstrenchcoat on tumblr) did most of the work this time around, I just set her off and wrote make out scenes. My tumblr is sassy-castiel, be sure to check us both out!**

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><p>That day, after Dean had fed his Pokémon and himself, they set off, heading towards Cerulean City. Along the way, they met many wild Pokémon and trainers alike. At one point, Dean even caught himself a Pikachu! He won all of the battles against the trainers he came across, and soon he neared Mt. Moon. Before he entered Mt. Moon, he saw some people in black clothing gathered around outside it, whispering to each other suspiciously. He shrugged it off, though, and made his way into the cave. Upon entering, he was surrounded by a swarm of Zubat and had to fight his way through them using his Pidgey as a deterrent. After he'd beaten the majority of them and scared the rest off, Pidgey seemed to glow, the light getting brighter and brighter until it lit up the cave. As the light dimmed, there was a newly evolved Pidgeotto hovering a couple of inches above the ground. "Awesome!" Dean exclaimed, running towards his beloved Pokémon. As he neared it, though, a Paras appeared as if out of nowhere, clicking its claws defensively. Dean stopped and pulled out his Pokédex. "Paras, the grass type Pokémon. Paras is a coconut crab-shaped insectoid creature, with the unique feature of having mushrooms known as tochukaso growing from its back. They grow from spores that are doused on this Pokémon's back at birth by the mushroom on its parent's back. The tochukaso can be removed at any time, although researchers suggest that Paras only do so under extreme measures." Dean looked at the Pokémon edging its way towards him and sighed. This would be too easy. "Pidgeotto, use Whirlwind!" Dean commanded. Pidgeotto stretched his new, significantly larger wings and flew to the ceiling of the cave, letting out an extremely strong gust of wind in the direction of the Paras, sending it flying off into the darkness. "Damn, that was easy." Dean chuckled as he picked up Pidgeotto's Pokéball and put it in his backpack.<p>

Slowly but surely, he made his way through the cave, only stopping to catch a Pokémon or check he was going in the right direction. As he neared the end, he was stopped by 2 people. A lady with unnaturally long, red hair that came to a curl at the end and a man with short blue hair and an unnaturally high voice, carrying a red rose.

"Prepare for trouble and make it double!" They said together, like they had rehearsed this a thousand times.

"To protect the world from devastation! To unite all peoples within our nation! To denounce the evils of truth and love! To extend our reach to the stars above!"

"Jessie!" the red haired lady took a small little curtsy.

"James!" the blue haired man threw the rose in the air.

"Team Rocket blast off at the speed of light! Surrender now or prepare to fight!"

"Meowth, that's right!" a Meowth appeared from behind them, doing a flip before standing on their shoulders in a perfectly choreographed way.

Dean blinked. Surely this must be a joke.

"I don't know who exactly you think you are-" Dean began, only to be stopped by Jessie's hand on his mouth.

"Hush, child." she said in a simpering voice. "Where exactly do you think you're going?"

"Well actually" Dean said, looking her up and down. "I'm prepared to go anywhere with you, darling." he winked at her and she stopped in her tracks before opening her mouth and closing it without saying anything.

"For a hot chick, you sure don't speak much. You're blubbering more than a Magikarp!" Dean laughed and tried to push past them but was stopped by the guy with blue hair, James.

"Now, you are going to give us all of your Pokémon or we will take them by force!" he threatened, although it didn't sound very threatening as he had the voice of a 12 year old girl.

Dean cocked an eyebrow. Was this guy for real?

"Well, you can try to take my Pokémon. But do you really think you'll win?" Dean said, always looking for a challenge.

"Koffing, go!" shouted James, throwing a Pokéball in the air and out came a purple Pokémon in the shape of a ball, hovering above the ground. Dean hadn't seen this Pokémon before so he consulted his Pokédex.

"Koffing is a round, purple Pokémon filled to the brim with toxic gases. Several crater-like protrusions on this Pokémon's body give it the resemblance of a naval mine or a meteorite. Koffing has a skull and cross-bones below its blissful face."

"Dude, if anything, your Pokémon looks high. What exactly have you been doing with it?" Dean said before turning to his Pidgeotto. "Ready for another easy win, buddy?"

Jessie then turned towards them.

"Ekans, attack!" she shouted with venom in her voice, releasing a Pokéball from her grip.

Dean also hadn't seen this Pokémon before so this was indeed a learning experience. He pulled his Pokédex out of his back pocket again and scrutinized it. "Ekans, the poison type Pokémon. Ekans live in grassy savannas and plains. It also inhabits cemeteries and moves quietly through grass. It is a very loyal Pokémon."

Dean withdrew a Pokéball from his backpack and threw it on the floor.

"Pikachu! I choose you!" with a flash of light, Pikachu was stood on the floor.

"Ha! You think you can beat us with a little rat and a pigeon? Please." Jessie giggled.

"You'll see." Dean smirked. "Pikachu, thunder shock!"

Pikachu contorted his little face in concentration and sparks of static electricity started forming at its cheeks before a blast of thunder rained down upon Team Rockets Pokémon, shocking them. Before Jessie or James could say or do anything, their Pokémon were down on the floor, paralyzed.

"Pidgeotto, blast them out of the cave!"

With wind strong enough to blow down a house, Pidgeotto flapped his wings rapidly, blowing the Pokémon and their owners like a candy wrapper caught in an updraft out of the exit of the cave. "TEAM ROCKET IS BLASTING OFF AGAIIIIIIIIIIIIIIIIIIIIIN-" was the last thing Dean heard of them. Chuckling, he made his way out of the cave, Pikachu perching cutely on Pidgeotto's back.

When they got to the Cerulean City Pokémon Centre, Dean realised how hungry he was. He left his Pokémon there so they could rest up and eat and went searching for a place to buy some decent food. When he walked into a Diner, appropriately named "Snorlax's Snacks", he spotted a cute blonde girl sitting in the corner on her own. Dean ordered a coffee and a bacon cheese burger and made his way over there.

"Hi, is this seat taken?" he flashed her his best smile and gestured to the seat in front of her. She looked up. "No, go ahead." she said, seeming alarmingly uninterested.

He took the seat and studied her. She had short blonde hair and bright brown eyes. "So, what brings you to Cerulean City, Mrs..."

"Masters. Meg Masters." she replies, looking at Dean curiously.

"Business, or pleasure?" said Dean, smiling at her yet again.

"Definitely business." she said, taking a sip of the coffee by her side.

"I'm sure I could put a little pleasure back into your life" Dean winked and leaned forward in his seat, unleashing his best "Come to bed" eyes.

She stood up abruptly and took her coffee. "Nah, I don't really like the desperate type." she swung her bag over her shoulder and promptly stomped out of the diner.

Dean sat back in his seat and sighed. Obviously, girls weren't as easy here as they were in his home town. He finished his cheeseburger and tipped the waitress before walking back to the Pokémon centre. He greeted his happy Pokémon and made his way to Nugget Bridge, where apparently there was a couple of Pokémon matches and if you beat all of the trainers, you won a prize.

Just as the bridge came within his sight, so did someone else. Walking down the bridge with an unhappy expression was Castiel Novak, clearly depressed and angry with something that went on beforehand. Dean stopped in his tracks and gulped, unsure of what to do. Castiel caught sight of him and turned a slight shade of red before making his way over there.

"Hello, Dean." Cas said, nodding his head.

"Cas." said Dean, nodding his in return.

"You wouldn't want to go up Nugget Bridge. It's all a scam, you win nothing" Castiel said, sighing and shaking his head. "Besides, all the Pokémon trainers are weak. Hardly a challenge."

Dean looked at Castiel before looking down at the Pokéballs at his belt.

"Hey, Cas, wanna battle?"

Castiel looked slightly taken aback.

"You want to battle me?"

"Why not? It's not like you could have gotten any worse since I kicked your ass last time" Dean smirked, remembering his previous battle with Castiel and remembering what happened in the shower after.

"You're on, Winchester!" Castiel replied, throwing down his bag before retrieving a Pokéball from his belt.

"Pidgeotto! Go!" Castiel cried, sending the Pokéball to the floor. With a screech, a Pidgeotto flew out and into the sky.

"Pikachu, I choose you!" Dean said, throwing his Pokéball in the air. In a flash of yellow light, Pikachu was on the floor.

"Pidgeotto, use gust!" Castiel commanded. His Pidgeotto flapped its wings rapidly, sending a burst of air towards Pikachu.

"Pikachu, dodge it and use Thunder Shock!"

Doing as his master said, Pikachu dodged the attack just in time before sending a bolt of lighting straight towards Pidgeotto, hitting it with stunning accuracy. Pidgeotto faltered a bit before regaining its height.

"Use sand attack, Pidgeotto, blind the Pikachu!"

Pidgeotto flew low to the ground and used its talons to send a spray of sand and mud directly in Pikachu's face before straightening back up and souring into the sky. Pikachu gasped in pain, rubbing his eyes to get the dirt out.

"Alright, Pidgeotto, gust now!" Pidgeotto sent out another burst of strong wind which picked the small Pokémon off the floor, sending it into the metal pole on the side of the bridge with a crack. Pikachu was down.

"Damn it, Cas!" Dean said through gritted teeth, he must have clearly underestimated Castiel's Pokémon. Dean withdrew Pikachu before picking up another Pokéball.

"Wartortle, come out!"

Wartortle stood, his stance low and ready.

"Wartortle, water gun!" Dean shouted, pointing at the Pidgeotto still hovering in the sky. Wartortle sent out a burst of water from its mouth quickly sending it Pidgeotto's way, but it was faster than that. It dived and collided with Wartortle, sending it to the ground. It bounced back up quickly though, sending another burst of water towards Castiel's Pokémon. It hit this time, sending Pidgeotto to the floor where it stirred before being still, clearly knocked out.

"Pidgeotto, return" Castiel put the Pokéball back in his bag before grinning at Dean. "That was only a taster, get ready for Charmeleon!" He threw another Pokéball to the ground and Charmeleon came out looking extremely intimidating.

Fire is weak against water, Dean thought. This should be a piece of cake.

"Wartortle, water gun again!" Dean shouted and Wartortle obliged, sending out a spurt of water and dousing the Charmeleon in it before it could do anything. Within ten seconds, the Charmeleon was out.

"Crap. This is crap." Castiel said quietly, not knowing Dean could still hear him.

"Rattata, go!"

Rattata came out in yet another burst of light.

"Rattata, hyper fang, go!" Castiel said.

Rattata ran towards Wartortle, jaw wide. It grabbed hold of it and bit down hard. But Wartortle's shell was harder. With a sharp crack, Rattata's teeth broke and he was sent back, paralyzed by the pain.

"Wartortle, tackle it now!" Dean said triumphantly, knowing he now had the match in the bag. Wartortle ran and collided with the Rattata, sending it flying. It hit the ground with a thump.

"Good job Wartortle!" Dean said happily, running over to his Pokémon and putting his hand up, waiting for him to do the same. This had sort of become their signature thing now. Dean straightened up before walking over to Castiel.

"Sorry about your Rattata, good game though, right?" Dean put out his hand. Castiel took it and gave it a brief shake before pulling on it so Dean and him were chest to chest.

Cas smirked, and leaned in, while Dean stood there, completely stunned. Castiel's eyes quickly flickered down to Dean's full, plump lips, and closed the distance between them and his lightly chapped ones. As soon as their lips met, Dean came alive, in a fit of passion. His tongue quickly snaked out, licking across Castiel's bottom lip, demanding entrance. Cas' mouth opened wide, sealing their lips together tightly, and Dean's assault of tongue was met by Castiel's. Their tongues entwined as they wrapped their arms around each other, attempting to be as close as possible. Castiel clawed at Dean's back, sending shivers down his spine. Dean reached down and grabbed Cas' ass, bringing their hips together in a rough, unpracticed movement. Their tongues tangled and fought for domination as they rutted against each other.

Then, as quickly as it had begun, it ended as Cas pulled away. Dean attempted to follow, nipping at Castiel's lip as he breathed a huff of laughter. He stepped away from Dean, who was a flushed, slightly sweaty mess, swaying slightly on his feet with his eyes still closed, breathing heavily.

"Sure was." Cas breathed. "But next time, I'm going to win." he smiled before walking away, leaving Dean stood there extremely flustered.

"You keep thinking that, buddy." Dean called and winked, recovering himself quickly before walking back over to his Pokémon, patting him on the head before putting him back in his Pokéball.

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><p><strong>TBC~<strong>

**P.S. We love you 3**


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